Gold‐Catalyzed Regioselective Oxyfluorination/Oxydifluorination vs. Diketonization of Phthalimido‐Protected Propargylamines with Selectfluor

Alkyl‐ and aryl‐substituted N‐propargyl phthalimides were used as valuable building blocks for the selective formation of the corresponding α‐fluoro, β‐phthalimido ketones, α,α‐difluoro, β‐phthalimido ketones or β‐phthalimido α‐diketones by means of gold‐catalyzed oxyfluorination/oxydifluorination o...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2022-08, Vol.2022 (29), p.n/a
Main Authors: Marsicano, Vincenzo, Arcadi, Antonio, Michelet, Véronique
Format: Article
Language:English
Subjects:
Chemical reactions
Diketones
Gold
Ketones
N-Propargyl phthalimides
Phthalimides
Quinoxalines
Reaction mechanisms
Selectfluor
Selectivity
α-Diketones
α-Fluoro-β-amino ketones
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Alkyl‐ and aryl‐substituted N‐propargyl phthalimides were used as valuable building blocks for the selective formation of the corresponding α‐fluoro, β‐phthalimido ketones, α,α‐difluoro, β‐phthalimido ketones or β‐phthalimido α‐diketones by means of gold‐catalyzed oxyfluorination/oxydifluorination or dioxygenation reactions. The key factors addressing the product selectivity control were determined. The simultaneous assembly of the quinoxaline nucleus and the removal of the phthalimido‐protecting group were tested. Reaction mechanisms of the different reaction pathways are assumed. The selective formation of α‐fluoro,β‐phthalimido ketones, α,α‐difluoro, β‐phthalimido ketones or β‐phthalimido α‐diketones is described by means of gold‐catalyzed oxyfluorination/oxydifluorination or dioxygenation reactions. The simultaneous assembly of the quinoxaline nucleus and the removal of the phthalimido‐protecting group were also performed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101524